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SYNTHESIS OF OPTICALLY ACTIVE gamma-VALEROLACTONE AND gamma-NONANOLACTONE VIA OPTICAL RESOLUTION USING CHIRAL AMINE DERIVED FROM AMINO ACID

  作者 YUMOTO KENICHI; HASEGAWA MORIFUMI; TOSHIMA HIROAKI  
  选自 期刊  Heterocycles;  卷期  2010年81-2;  页码  421-431  
  关联知识点  
 

[摘要]Optically active gamma-valerolactone and gamma-nonanolactone have been synthesized via optical resolution using a newly developed chiral airline derived from L-phenylalanine. Both racemic gamma-lactones were transformed to corresponding diastereomeric amides by amidation with the optical resolution agent. Fractional crystallization of diastereomeric amides, recrystallization of each diastereomer, and Subsequent hydrolysis gave optically active gamma-valerolactone and gamma-nonanolactone with Sufficient enantiomeric excess and isolated yield. The optical resolution agent was recovered after hydrolysis.

 
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